Ranking the 15 Most Boastful Tennis Players of All Time

Tennis is a game of finesse, strategy, and mental toughness—but let’s be real, a little swagger never hurts. Some players walk onto the court with such overwhelming confidence, it’s almost a weapon in itself.

Whether it’s chest-thumping celebrations, spicy quotes in press conferences, or just an undeniable air of “I’m better than you,” these players didn’t just back up their game—they talked it, too. Here are the 15 cockiest tennis players of all time, ranked from bold to full-on brash.

15. Fabio Fognini

Fognini plays with flair and talks like he’s the main character in every match, win or lose. His fiery temper and flashy game make him must-watch, even when he’s blowing a gasket.

14. Jelena Ostapenko

Ostapenko swings like every shot is a winner and argues like every call should go her way. She brings a boldness to the court that’s as entertaining as it is unpredictable.

13. Daniil Medvedev

Medvedev’s deadpan humor and sarcastic interviews have become legendary. He knows he’s good, and he makes sure the crowd knows it too—especially when they’re booing.

12. Ernests Gulbis

Gulbis once said most players on tour were boring and uneducated, which tells you everything you need to know. He never had a filter and always believed his game was miles above his ranking.

11. Lleyton Hewitt

Hewitt’s “C’mon!” celebrations and in-your-face energy made him a player fans either loved or loved to hate. He strutted around the baseline like he owned it—and for a while, he did.

10. Serena Williams

Serena didn’t just beat her opponents—she made sure they felt it. Her presence, stare-downs, and supreme confidence were unmatched, and she earned every bit of it.

9. Marat Safin

Safin had a monster game and the ego to go with it. He could destroy a racket or charm a reporter with the same effortless swagger.

8. Roger Federer

Yes, Federer was polite and smooth—but don’t be fooled, he knew he was the gold standard. That calm exterior masked the quiet confidence of a guy who walked in expecting to win every single match—and often did.

7. Bernard Tomic

Tomic once admitted he played purely for money and didn’t care what anyone thought. His complete lack of filter and casual arrogance made him one of the most frustratingly cocky players ever.

6. Gael Monfils

Monfils plays to entertain, and he knows exactly how cool he looks while doing it. He’ll try trick shots mid-rally just because he can, and somehow pull them off with a grin.

5. Nick Kyrgios

Kyrgios might be the king of tennis trash talk in the modern era. He mocks opponents, beefs with fans, and somehow always believes he’s the best player in the world—even when he’s barely practicing.

4. Jimmy Connors

Connors was a showman with a snarl, and he loved to rile up crowds and opponents alike. He thrived on being the villain and never missed a chance to let everyone know how great he was.

3. Andre Agassi

Young Agassi didn’t just play tennis—he rockstarred it. The long hair, the denim shorts, the anti-country club attitude… he oozed cool and knew it.

2. Novak Djokovic

Djokovic feeds off doubt, dances with controversy, and always walks with the air of a man who believes he’s the best—because he often is. His unapologetic confidence has made him both iconic and polarizing.

1. John McEnroe

Nobody threw tantrums with more style than McEnroe. His meltdowns were legendary, but so was his belief that no one could touch him on the court—just ask the umpires he yelled at.